Entire home

Waterfront. Private beach. Pool. Estate has it all!!

Photo gallery for Waterfront. Private beach. Pool. Estate has it all!!

A covered outdoor seating area with wicker furniture, a table, and a view of a lake and trees.
A large, elegant house with a gravel driveway and a well-maintained lawn.
A kitchen with a refrigerator, stove, microwave, and cabinets.
A pool table in a room with white walls, large windows, and wooden chairs.
A room with two beds, a chair, and a table.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Unmatched views, unforgettable moments
    Guests like the location for the scenic views.

Popular amenities

  • On beach
  • Private pool
  • Patio
  • Dog-friendly
  • Toys
  • Barbecue grill

Explore the area

View in a map
Orleans, MA
  • Place, Cape Cod Beaches
    ‪6 min walk‬
  • Place, Chatham Lighthouse Beach
    ‪19 min drive‬
  • Place, Cape Cod National Seashore
    ‪21 min drive‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪38 min drive‬

Rooms & beds

9 bedrooms (sleeps 19)

Bedroom

1 Queen Bed

Bedroom

2 Single Beds

Bedroom

2 Single Beds

Bedroom

1 Queen Bed

Bedroom

2 Single Beds

Bedroom

1 King Bed

Bedroom

2 Single Beds

Bedroom

3 Single Beds

Bedroom

1 Queen Bed

5 bathrooms, 1 half bathroom

Bathroom

Bathtub or shower · Toilet

Bathroom

Toilet · Shower only

Bathroom

Bathtub or shower · Toilet

Bathroom

Toilet · Shower only

Bathroom

Toilet

Bathroom

Bathtub or shower · Toilet

Bathroom 7

Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Garden
Dining area

Add dates for prices

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About the area

Orleans

Located in South Orleans, a neighbourhood in Orleans, this holiday home is near a water park and on the beach. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Academy of Performing Arts and Orleans Bowling Center are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.
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Map
Orleans, MA

What's nearby

  • Cape Cod Beaches - 6 min walk - 0.5 km
  • Chatham Lighthouse Beach - 19 min drive - 15.1 km
  • Cape Cod National Seashore - 21 min drive - 15.4 km
  • Mayflower Beach - 38 min drive - 35.2 km
  • Hyannis Harbor - 39 min drive - 40.7 km

Getting around

  • Hyannis Transportation Center - 31 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 38 min drive

Restaurants

  • ‪Three Fins Coffee House & Cacao Factory - ‬12 min drive
  • ‪Jo Mama's - ‬9 min drive
  • ‪The Barley Neck Inn - ‬11 min drive
  • ‪Dunkin' - ‬11 min drive
  • ‪Outer Bar And Grille - ‬8 min drive

Frequently asked questions

Does Waterfront. Private beach. Pool. Estate has it all!! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Waterfront. Private beach. Pool. Estate has it all!! pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Waterfront. Private beach. Pool. Estate has it all!!?

On-site parking is available at the property.

What time is check-in at Waterfront. Private beach. Pool. Estate has it all!!?

Check-in begins at 3:00 PM.

What time is check-out at Waterfront. Private beach. Pool. Estate has it all!!?

Checkout is at 10:00 AM.

Where is Waterfront. Private beach. Pool. Estate has it all!! located?

Nestled on the beach, this South Orleans holiday home is within 3 mi (5 km) of Cape Cod Beaches, Captain's Cove Golf Course and Captains Golf Course. Nickerson State Park and Pilgrim Lake are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 34 out of 35 reviews
Rating 8 - Good. 0 out of 35 reviews
Rating 6 - Okay. 1 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

8.0/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect in every way!

The Winslow estate was the perfect spot for our family vacation. Three generations enjoyed every aspect of the property. Ken and Ginger were a pleasure to work with.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 11 Jul, 2022
Thank you. It was a pleasure having your family here.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Own Beach & Pool

Amazing hosts on an amazing property!! Beautiful views and attention to small details - like the clean linen was on the bed for us!! And the welcoming basket!! Thanks so much for the memories!!
Stayed 7 nights in Aug 2024
Response from VrboOwner on 22 Aug, 2024
Thank you Korery - you were a wonderful family to have here.
Archival

10/10 Excellent

Gorgeous Views on the Water for peace on The Cape

Three generations of our family spent a lovely week at the Gentle Heritage in late August. The views are spectacular of the water and surrounding land, and has a nicely-manicured lawn on which to play games while surrounded by the beauty. We could walk down the hill to enjoy a little seating area just above a small beach to launch our kayak. The home is cool in its long extended layout which reminds us of its history, with 2 kitchens and a joined wing that has its own suite and glassed in porch, tv room and dining are. Favorite spots to hang out were in the billiard room, another large screened porch overlooking the water off the Master bedroom and the main living room with it's high ceiling and architectural beams. We also enjoyed an outdoor dining patio and lounge chairs on the lawn to gaze at the stars. The property has a good number of bedrooms and bathrooms to be used by the 12 in our group. The owners also provided information for a local chef who prepared a glorious meal at the home for us...highly recommended. Definitely worth a stay for relaxation and a great spot on The Cape!
Verified review

6/10 Okay

Liked: Check-in, communication, location
Disliked: Cleanliness
The location, privacy, views, and grounds are outstanding. The house is large and rustic, with recently remodeled bathrooms but other areas that show its age. Since our stay, the listing has been updated with a floor plan. After booking a 9-bedroom home we were surprised that two are enclosed lofts only accessible through adjoining rooms. This was an issue for our group.All 11 split A/C units had mold. The host responded quickly and had them cleaned during our stay. Disruptive for us, but good for future guests. There were ants and mice in the kitchen. The main refrigerator was broken. (If a house comes with a note in the kitchen explaining how refrigerators cool and with instructions not to adjust the temperature, it’s clear there is a known issue.) Per the instructions we spent the first couple of days waiting for the fridge to work. We ended up tossing our perishables and moving everything to the second fridge.The house didn’t feel clean: bathmats appeared vacuumed but not laundered, shower curtain and tub mat were stained, the toaster had not been emptied, and we found a pair of briefs on a lamp when we checked in. Upholstery and carpeting felt grimy, radiators were dusty, and the laundry room was cluttered and unkempt.That said, we recognize the challenges of maintaining an aging seaside estate. The host, Ginger, was gracious, responded promptly to issues, and provided a partial refund. With improvements, this could be an exceptional property.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 5 Sept, 2025
It has been a hot and humid summer on cape cod. Perfect for using our pool and visiting the beaches. But, it made it tough on mold control on the AC. As soon as we heard of this problem, we had a tech there the next day. As soon as we heard of the refrig, we had a tech there in a few days. The house has a secondary refrig and we offered a replacement refrig, but the guests declined. The refrig is 3 years old, cost over $10,000 and has been problematic this summer. A 1k replacement part has now been installed as the manufacturer has come up with a fix for all of this model. Ants and mice will happen, but we had a handy man on site a few hours after we were notified. Our cleaning team is 5 experienced women. Then we have a 4 person linen team. We as the owners work closely all day with these people. Bath mats, comforters, shower curtain are replaced weekly or biweekly. There are extras available if people want to change them out. We have no idea where the briefs on the lampshade came from.... With all the other 5 star reviews it is always helpful to hear these things. We do try our very best to make sure all is well.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway in the year of Covid!

This property is just as stunning and beautiful as the pictures show. We were at maximum capacity with 19 people (4 families) and we never once felt crowded or that we didn’t have enough room. Amazing. Loved the historic nature of the house that’s over 100 years old but that also included modern updates where it mattered the most (bathrooms, beautiful new pool). With Covid we barely left the property but you didn’t have to!!! Such a fun and relaxing week. We felt like we were the Kennedys on the compound for a week! Ken and Ginger were very responsive to any questions or issues. Highly recommend.👍
Stayed 7 nights in Aug 2020
Response from VrboOwner on 25 Aug, 2020
Thank you so much Laura. You were a wonderful family to have at the property. Your family was always very communicative and left everything spotless. Much appreciated.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

About as good as it gets for large families

We were looking for a place that could accommodate our extended family and friend’s reunion on Cape Cod. Ken and Ginger’s historic home overlooking Pleasant Bay was exactly what we were looking for. The house absorbed the comings and goings of 25 guests over the two week stay. The location was breathtaking, the house met our needs and Ken and Ginger couldn’t have been more accommodating. Nothing is perfect. The house is a bit funky and looks more like a Bermuda cottage resort than Cape Cod, but it’s clean, well equipped, beautifully situated and everyone thoroughly enjoyed being there. If I could change anything it would be to add another bathroom or two. Nine bedrooms and 5 bathrooms require some flexibility, but we made it work. We recommend it highly to anyone planning an important family event.
Stayed 14 nights in Aug 2019
Verified review

10/10 Excellent

Fantastic Property!

Our Bookclub of 6 couples stayed at Ken and Ginger's home this past weekend. We found the homeowners to be a pleasure to work with and each one of us had a great time. The home is well appointed with plenty of space and a fantastic water view with many areas to gather or find space if you need to. The kitchen and dining room easily held all of us. The pool table and dart board were a nice bonus!
Stayed 2 nights in Nov 2018
Verified review

10/10 Excellent

Incredible Location & Home!!

We brought the entire extended family to celebrate our parents' 50th wedding anniversary and we could not have been happier with Gentle Heritage. The home is enormous, giving everyone the space they needed and also the common areas to all meet up for meals, chatting or just enjoying the incredible views of Pleasant Bay. The house is up to date, charming and we could not have asked for a better location. The Winslows were very attentive to our needs and made for very gracious hosts. We ranged in ages from 5 to 75 and the home worked for all of us. The private beach was so great for days we didn't want to leave the compound...and we found that we really didn't need to as we had everything we needed at the house. We were all very sad to leave, but plans to return are already in the works! Thanks again to the Winslows for sharing their amazing home with us. A trip to remember!
Stayed 6 nights in Aug 2018
Response from VrboOwner on 26 Mar, 2020
Thank you so much. It is always wonderful to know families have had a great vacation. You all were perfect guests.
Archival

10/10 Excellent

Outstanding property and owners

Must concur with the rave reviews of others. Gentle Heritage estate is unique and magnificent. Gorgeous grounds in a prime Cape Cod location. Ginger and Ken could not have been any kinder in all of their communications and accommodations. Highly recommend this estate and you can rest assured that it will be a pleasant experience with the Winslows.
Stayed 3 nights in Nov 2017
Archival

10/10 Excellent

An epic landscape bedecked by a unique jewel

A superb venue; a persistent rain the first day couldn't dampen the great fun experienced by 6 couples while staying for a get-away at this magnificent property. The charming accommodations, fine food, many nearby leisure pursuits and breath taking vistas of the wild beauty of Cape Cod were only exceeded by the warmth & genuine hospitality of the Winslows.
Archival

10/10 Excellent

To call it spectacular doesn't even do it justice!

I rented the Winslow Estate for my daughter's wedding. Renting from Wednesday to Wednesday gave us all time to get settled in and time to relax after the fact. As I stated above to call the estate spectacular is truly an understatement. Everything was as promised. Ken & Ginger were great to deal with. I would strongly recommend this property to anyone. A little piece of heaven on Cape Cod!
Archival

10/10 Excellent

Perfect venue to have a personalized wedding

If you're looking for that special place to hold your wedding, look no further. Unlike a resort venue with packaged plans, at the Winslow Estate you can make your wedding your own. The owners, Ken and Ginger, are eager to help you pull the pieces together with suggestions and lists of auxiliary vendors. Don't be deterred by the idea of an afternoon wedding. Nothing was more romantic than the tent coming alive for dinner and dancing after enjoying mid afternoon cocktails and fantastic views of Pleasant Bay in the bright sunshine. Not to mention the brilliant sunset enjoyed by all the guests! There was plenty of room for the entire wedding party and spouses to stay at the estate and they enjoyed their own post-wedding hang time together in a very relaxed, fun space. The Winslow Estate is the perfect wedding venue!
Archival

10/10 Excellent

Exquisite, Fascinating!!

My husband and I have stayed there for my birthday. We had a fantastic time! The owners ken and ginger are awesome and were very accommodating to our needs. We had a great time. We are planning on coming back here again next summer.
Archival

10/10 Excellent

Absolutely picturesque

Whether you are looking for the ideal Cape Cod wedding venue or a private rental for a week-long vacation, this property is perfect. The setting (right next to the water on Pleasant Bay in Orleans) is stunning, beautiful, relaxing and, quite simply, breath-taking. We were blessed with 6 straight days of gorgeous sunshine and warm temperatures - making this the most memorable vacation of our lifetime. You will not be disappointed!
Archival

10/10 Excellent

A Beautiful Place!

From the moment we stepped on this property, with its magnificent, panoramic view of the bay, we knew it would be perfect for our daughter’s wedding. We had visited all the best venues on the Cape and this place was special. We rented Gentle Heritage for a week and arranged for the entire wedding party to stay with us. The owners were very pleasant, organized and helpful with logistics before the wedding. With plenty of rooms and lots to do on the property, we all had a fantastic time. Gentle Heritage has great facilities, spacious common rooms, many bedrooms and bathrooms, two kitchens, a billiards room, big backyard, and two pathways leading down to the beach. The bedrooms are well-appointed and comfortable. A family member brought his boat (there is public boat access nearby) and a few of us had a great time boating around Orleans and Chatham. The wedding was fabulous. So many of our guests commented that the property was the most beautiful they had ever been to for a wedding. With its breathtaking view of the bay and surrounding area, and perfect summer weather, it was truly a special day.
Archival

10/10 Excellent

Breathtaking, one of a kind home

This house is incredible. My husband and I recently got married at the house. We had our closest friends and family stay with us for a week. All of our wedding guests were blown away with the views. The house has plenty of bedrooms and hangout space. It is also easy to access the water. We cannot wait to go back and spend anniversaries there.
Archival

10/10 Excellent

Gorgeous views, spacious home, a MUST stay!

Wow. Gentle Heritage has everything you need for a memorable stay on Pleasant Bay! This home delivers on everything in the summary, other renters’ reviews, and so much more. Gentle Heritage is very spacious and allows for multiple activities to happen at the same time or you can all hang out together in the living room or, even better, the beautiful outdoor space. The view is absolutely spectacular and I recommend enjoying it as often as possible during your stay. I rented the property for a full week and it also hosted my 75 guest wedding. It could not have been more perfect. With so many rooms the Bride and Groom can each get ready at the house without the risk of seeing each other beforehand. The yard overlooking the bay makes for the best location for both ceremony and reception. Walking down to the deck by the beach makes for breathtaking photos. So much of the estate will become a part of your special day. The owners are so helpful! Whether just staying with your family for the week or trying to plan a wedding, they are quick to respond to any message and accommodating your unique needs. They made our stay everything we wanted it to be, and more.
Archival

10/10 Excellent

Unique, special and excellent wedding venue!!

I take full credit for finding Gentle Heritage, Winslow Estate. Being an owner of a second property on Cape Cod, my daughter felt that her wedding should be on the Cape since we are on Cape as much as possible during the year. Besides the location and the property being so unique and gorgeous, especially when you have a day like we had weather-wise, the fact that the wedding party gets to stay there days before the wedding and after if they so choose is a bonus!! I truly believe that this allowed the wedding party to bond before the big day. It was also nice that we were the only wedding going on at the venue, unlike most places we looked at. We were constantly asked throughout the day, "how did you find this place" so we were thrilled with how everything turned out. So, from a wedding standpoint, it's a 10 in our opinion.
Archival

10/10 Excellent

A wonderful family holiday at Gentle Heritage

In our family's week long stay at Gentle Heritage we were sixteen ranging from 92 to 18 and unanimous in our enjoyment of the house, its location, views, comfort and amenities. We have stayed in large vacation homes in about ten different countries but this house tops them all. Loet V. Sheffield, MA
Archival

10/10 Excellent

The perfect spot for a group getaway or retreat!

This was the second year that our group of nine adult women--all artists and/or writers--gathered for a long spring weekend at this gorgeous waterfront property. We knew from our first visit that the property is, if anything, even better than described: secluded yet not too remote, spotless, well-maintained, and spacious, with plenty of room to spread out. We each had our own charming bedroom for reading, writing, and napping; we also made full use of the shared spaces, such as the TWO fully stocked kitchens, the porches, the sunroom, and the living rooms, where we worked on projects, played games, or just hung out together. The owners are friendly, professional, and, above all, responsive. We expect to make this getaway an annual tradition at this venue, and some of us have already recommended it to friends and relatives. It's a real treasure.
Archival

10/10 Excellent

The Winslow Estate was the perfect venue !

The Winslow Estate was the most magical venue to hold our daughter and son in law's wedding! The kind hosts were most accommodating with any of our needs! Our guests flew in from all over the world and everyone was so taken back by the beautiful setting! We will cherish our memories of this very special event in our lives!!! Paul & Denise Graves
Archival

10/10 Excellent

Spectcular Property

Gentle Heritage is an absolutely spectacular property! The views from the bluff over-looking Pleasant Bay are gorgeous. Everything was very clean and well maintained. We were there for a family wedding (held elsewhere), so it was a perfect place for so many of us to gather for the weekend. Luckily, the weather was perfect and several people even enjoyed a dip in the water. The listing description was accurate and the owners were very helpful and accommodating. I highly recommend this property!
Archival

10/10 Excellent

Unforgettable Wedding Location!

Although my fiancé and I are not from Cape Cod, we knew as soon as we got engaged that the Cape was the perfect destination for our wedding. Despite residing in Chicago we researched from afar and narrowed our selection to 10 different venues/locations to visit the following month. Although we saw some amazing places, we knew in our heart the winner would be the Winslow Estate and upon arriving for our tour and driving up the entrance way, our decision was instantly made even before we got out of the car. Our criteria was simple: we wanted our ceremony and reception at the same location, preferably outside, where our wedding party was also able to stay through the weekend and the Winslow Estate accommodated all the above. To say the estate is beautiful is a complete understatement. The house itself, the yard, the views of Pleasant Bay are all breathtaking. Although I’ll admit the price was a bit of a surprise at first, we can say now it was 100% worth it. Once we decided that the Winslow Estate was right for us, the owners (Ken and Ginger) were incredibly helpful, responsive and supportive throughout the entire planning process; always available to answer questions via phone or e-mail or provide recommendations as needed. Given that we were planning a wedding from Chicago, this level of support was certainly needed! We were able to have ourselves and our entire wedding party sleep and stay at the estate leading up to the wedding. We had a smaller guest count (around 85) that all fit comfortably during both the ceremony on one side of the yard and then under a covered tent during the reception on the other side. I’d recommend the Winslow Estate to anyone without hesitation whether for weddings, family reunions, etc. Our memories from our wedding day are priceless, largely due to the location we held it at. Thank you Ken and Ginger for an amazing experience!
Archival

10/10 Excellent

Amazing week

The Gentle House was amazing for my wedding week. My husband and I were able to move in Wednesday and start the preparation for our wedding day that was on Saturday. My whole family came on Thursday and enjoyed the luxuries of the house and the beautiful scenery. The house was the perfect size for the 18 of us because we were not on top of each other and there was plenty of space to relax or enjoy the outdoors. The house had EVERYTHING you need for the week like linens, kitchen needs, laundry, games, beach toys, and cable / Internet. Everybody who attended the wedding could not believe the unbelievable view over the water and the amenities the house provided (clean bathrooms and patio to converse on). Ken and Ginger were a pleasure to work with and were very accommodating with anything needed. The week was amazing and well worth the cost of renting for the week. Mike and Kate
Archival

10/10 Excellent

Absolutely BEAUTIFUL!!

We spent a fabulous week at Gentle Heritage with the whole family...age range 5 yrs old to 75! We have rented other homes on the Cape over the years and especially enjoyed our stay here. Ken and Ginger take such good care of the house and property with attention to the details. Each room is comfortable, clean, and very nicely decorated. We did a fair amount of cooking and were happy that the kitchens were well equipped. The two upstairs rooms are very charming and have beautiful views of the property and the bay! I love that there were fresh flowers on the table when we arrived! We swam and went kayaking on the bay, played pool, relaxed in the lounge chairs on the patio and sat in the evening just looking at the stars. The property is big enough for everyone to have their own space and our hosts were so helpful with anything we needed but not at all intrusive. We took their recommendation and had a chef come to cook for us two separate nights of our stay. What a treat!! It's hard to go out with 19 people and having someone come prepare a wonderful meal was perfect! They also clean it up! This property is unlike any other on the Cape. Such a grand home and a spectacular view. It's no wonder so many people have chosen to get married here. We enjoyed every moment of our family vacation and would love to come back again. Thank you Ken and Ginger!
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